Efficient N-Trifluoromethylation of Amines with Carbon Disulfide and Silver Fluoride as Reagents

IF 9.4 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY CCS Chemistry Pub Date : 2024-08-06 DOI:10.31635/ccschem.024.202404432
Haixia Song, Qin Wang, Xiaoying Wang, Yinbin Zhang, Xin-Hua Duan, Mingyou Hu
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Abstract

The installation of a trifluoromethyl group onto a nitrogen atom can effectively modulate the basicity of amines owing to the strong electron-withdrawing effect of fluorine. Nevertheless, efficient and operationally simple methods for N-trifluoromethylation of amines are yet to be developed. This protocol involves the use of readily available secondary amines as starting materials, along with CS2 and AgF as the N-trifluoromethylation reagents, enabling the target molecules to be synthesized in a single step. The versatility of our method was demonstrated by successfully synthesizing N,N-dialkyl and N-(hetero)aromatic N-CF3-containing compounds with various substituents. Moreover, this methodology has been successfully applied to the late-stage modification of complex bioactive molecules, facilitating the synthesis of N-CF3 drug bioisosteres and N-CF3-tailored amino acids, which would broadly stimulate the drug discovery of N-CF3 containing molecules.

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以二硫化碳和氟化银为试剂高效进行胺的 N-三氟甲基化反应
由于氟的强夺电子效应,在氮原子上安装三氟甲基可以有效地调节胺的碱性。然而,高效且操作简单的胺 N-三氟甲基化方法仍有待开发。本方案以容易获得的仲胺为起始原料,以 CS2 和 AgF 为 N-三氟甲基化试剂,从而能够一步合成目标分子。我们成功合成了含有各种取代基的 N,N-二烷基和 N-(杂)芳香族 N-CF3 化合物,证明了我们的方法具有多功能性。此外,该方法还成功应用于复杂生物活性分子的后期修饰,促进了 N-CF3 药物生物助剂和 N-CF3 定制氨基酸的合成,这将广泛推动含 N-CF3 分子的药物发现。
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来源期刊
CCS Chemistry
CCS Chemistry Chemistry-General Chemistry
CiteScore
13.60
自引率
13.40%
发文量
475
审稿时长
10 weeks
期刊介绍: CCS Chemistry, the flagship publication of the Chinese Chemical Society, stands as a leading international chemistry journal based in China. With a commitment to global outreach in both contributions and readership, the journal operates on a fully Open Access model, eliminating subscription fees for contributing authors. Issued monthly, all articles are published online promptly upon reaching final publishable form. Additionally, authors have the option to expedite the posting process through Immediate Online Accepted Article posting, making a PDF of their accepted article available online upon journal acceptance.
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